Fit The First

It should never have happened the way it did. It really probably shouldn’t have happened at all.


But it did.

I was driving home from school after Math Bowl one cold and raw afternoon in January, when I saw Mr. Stephenson slouching along the side of the road, all six foot seven of him, bent over and huddled down against the bitter wind.

I pulled over and opened the passenger side, and he folded himself gratefully into my car, like a giant origami swan.

His knee pressed up against my thigh, almost certainly because he didn’t have any room, but the contact gave me an instant hard-on.

I had, of course, jerked off to Mr. Stephenson before. But then again, I had probably jerked off to everyone in my school, student or staff, male or female. I was an oversexed teenage math geek.

Choosing to interpret the cramped conditions as flirtation, I placed my hand on Mr. Stephenson’s thigh, a few inches south of the crotch. He responded by putting his tennis racket sized hand on top of mine, and our fingers intertwined. The temperature inside the car rose a couple degrees.

I parked the car in front of Mr. Stephenson’s house, a shabby-looking beige duplex at the end of a cul-de-sac. I could see a promising-looking bulge in the front of his slacks. I leaned over and kissed him on the lips.

“I’ve never done this before.”
“What, fooled around with a student?”
“No, kissed a guy.”

For all that he was a pretty good kisser. It wasn’t exactly my first time. I’d fooled around more than once, at math camp and on sleepovers, with guys and with girls, giggly, embarrassing half-acknowledged gropings. This was a different order of magnitude altogether.

We unfolded ourselves from the tight confines of the car and jogged up the walk to his front door. He fumbled his keys out of his pocket, dropping them on the stoop, rattling them in the lock, before he finally got the door open, and then we more or less fell inside, letting the door slam behind us. I pretty much attacked him, tearing his pants off and freeing his raging cock.

It was bigger than I had imagined, but not so big as to be scary. I thought it looked incredibly sexy. He was uncircumcised, and the livid purple head peeked sassily out from under his foreskin. I started kissing and nibbling him, licking all up and down the shaft and around the head, playing with his balls. He had a nice taste. His dick was so hard it was literally quivering.

Any qualms Mr. Stephenson may have still had about fooling around with an underaged male student were left crumpled up on the floor alongside his trousers and briefs. He reached inside my shirt, rubbing and pinching my erect little nipples as my head bobbed up and down on his cock. It didn’t take him very long. With my lips wrapped around his dick like a big, hot popsicle, I reached under his fat ball sac and tickled his anus, and he shouted out loud, grabbing my hair and crushing me into his crotch, exploding in my mouth, filling my mouth up with hot, sticky, salty-bitter semen. I swallowed every drop.

He sucked my dick next, but I have to tell you he wasn’t really very good at it, not that first time anyway. I ended up straddling his chest and jerking off onto his face as he tentatively slipped one saliva-slick finger up inside my tight and slightly nervous, but very horny asshole.

We fooled around a lot more that semester, but we never actually fucked, for reasons I still don’t quite understand. It turns out Mr. Stephenson had a girlfriend, and I really wanted to do a threesome with her, but he was worried that she wouldn’t be into it, which was kind of ironic, because later on I did end up fooling around with her too. She taught me a few tricks that I still use today.

I guess I expected things to be weird between us after all that, in class and whatnot, but honestly it wasn’t weird at all. Life went on, the world kept turning, and in due course I graduated and moved on.

It almost didn’t happen at all that day. We had planned it out in advance, but then It started to snow, and your husband wasn’t sure he wanted to be out driving in that stuff.


But you convinced him to go anyway.

As soon as I got your text, I felt my pussy start to salivate. I had been playing with my clit all morning, idly browsing porn and thinking about what we were going to do. I sprinted to my car and drove to the mall.

I bided my time, looking in store windows and watching people, bored teens and old folks. I hadn’t worn any panties on purpose, and I felt naughty and very aware of my naked, horny cunt just under my short black skirt.

I caught a glimpse of you and your husband. He looked not at all as I had imagined him: older, dumpier, somehow diminished. Middle-aged. You looked simply radiant.

I saw you talking to him. After a brief discussion, you two parted ways. He went into a sporting goods store. You went into H&M.

About two minutes later you texted me again. That was my cue. I went into the H&M, pulling a few shirts and bras off the racks totally at random, and headed toward the fitting rooms. You were in the last one on the left.

I tapped on the door, and you opened it. I stepped inside, closing and locking the door behind me. This was the first time we had seen each other in person. I dropped my armload of clothes on the bench, and hugged you tight, kissing your pretty lips. I felt your hands on my ass, pulling me closer.

I dropped down on my knees, tugging your panties down. Your pants were already off. We had to be efficient, time was at a premium. I gave your pretty pussy a perfunctory kiss, then dove in, licking up and down and all around, trying to apply all the lessons I’d learned from watching porn and reading dirty stories.

I’d been a little afraid I wouldn’t like the taste, that the flavor of another woman’s pussy would be repulsive to me. I shouldn’t have been worried. You were intoxicating, clean and sexy, musky and feminine. With a little help from your guiding hands, I found your clit, circling your swollen little nub with my outstretched tongue.

I looked up to see if I was doing a good job. You had pulled your bra down, and your big tits bounce free, nipples erect and pointing out in disparate directions, Your eyes were closed, your head thrown back, and you were chewing on three fingers of your own hand. I guessed I was doing ok.

I felt you come. Your whole body seemed to go rigid, and then your stomach pulsated and your pulled me in hard. I couldn’t breathe for a long moment there, but I didn’t mind. Then you lifted me up and we were kissing. Your juices were smeared all over my face.

I turned around, facing the mirror so I could watch what you were doing. It was your turn to get down on your knees. You licked my asshole, just like you had promised in your emails, fingering my pussy deeply as your tongue probed and explored my virgin little hole. I rubbed my clit, savoring the sights and sensations, saving the memories up for later use. I made myself come quickly, resisting the urge to draw it all out, giving myself a silent little orgasm. There would be more later on, after I got home. Maybe I’d make you a video.

I’m not sure how long we had been in there, maybe five minutes. It already felt like too long. We got paranoid; kissed one more time, and then you pulled your pants on, tucked your tits back in, and left the dressing room. I got myself dressed, counted to seventy five, and headed out, dropping the clothes I’d picked up in a cart full of shirts, pants, and bras.

I saw you one more time as I headed for the parking lot. You were walking hand in hand with your husband. He was looking at his smart phone, totally unaware that my come was still drying on your face and fingers, that I was still wet from your affection.

I drove home, touching my pussy in the car as I drove, thinking about you the whole way.

We weren’t even supposed to meet yet, not for another two weeks.


But… the doctor at your office got sick. He came in late, saw two patients, sneezing and hacking and snuffling the whole time, and threw in the towel. “Close the place down,” he said, “Pay yourselves for the day, I don’t care. I’m going home.”

When you texted me, I had just put my son on the school bus. “Of Course!” I replied, “Where can we meet?”

I wound my way down the Taconic, dirty piles of snow looming on either side of the twisty highway, keeping the speedometer needle exactly five miles above the speed limit, fighting the urge to speed like a maniac, like a bank robber, like a cheating husband.

You were already in the donut shop when I arrived. You were sitting in a corner booth, sipping coffee from a paper cup, a multi-colored torus covered with sprinkles sitting untouched in front of you. You looked just as sexy in person as you did in your pictures. I don’t know why that should surprise me, but it did. My cock was hard inside my pants.

I sat down across from you. There was a momentary awkward silence as we both took a breath, preparing to speak. I had never heard your voice and you had never yet heard mine.

“Was the drive OK?”
“It was fine,” I said. “It’s so good to finally see you in person.”
My hand reached out across the table and our fingers intertwined. The awkwardness faded away like a mist off melting snow.
“Let’s get out of here,” you said. “I don’t want to waste any of our time together.”

In your car in the parking lot, out behind the donut store, between the dumpster and the train tracks, I leaned across to kiss you. Your lips met mine like an electric shock. My hand found your thigh, squeezing and caressing as your tongue entered my mouth. We kissed for a long time, I don’t know how long, long enough to fog up all the windows. Your hand started rubbing my erect cock through my pants. I could feel your hot dampness through the fabric of your jeans. My cock was straining hard against its confines, so hard it almost hurt. My hand traveled up, cupping your large, soft breast.

You took my hand in yours, guiding it up under your shirt, inside your bra, where I found your nipple, hot and swollen. I pinched, gently and first, then harder, enjoying your squirms as I nibbled on your neck.

“Please,” you moaned, “Please, please, please…”

Your jeans came down, a wrestling match in the tight confines of the driver’s seat of your car. My own pants came off as well, almost as an afterthought, much easier without a steering wheel in the way. My cock made a giant tent in the front of my boxers. Your bright red panties were visibly wet, almost like you had peed yourself.

You reclined your seat all the way, and I lay my head in your lap. The smell of your sex was intoxicating, your pussy moist and pink and open. I stuck my tongue out, savoring that first taste, the salty musky flavor that is all your own. You made a noise, hands curling in my hair. My tongue found your clitoris, swollen and eager as my fingers probed inside your hungry pussy. You were already moaning, humping back against me. This was clearly not going to take long.

Two fingers up inside your pussy, rubbing hard against that special spot, my tongue pressed hard against your clit, another finger just tickling your asshole. You came, and you came hard, grinding against me, crying out loud as your body bucked and shook. I stayed with you through to the very end.

Finally I came up for air. My face was coated in your juices, my fingers covered in it. I lick my fingers clean, and you kissed my come-slick lips again and again, hand wrapped firmly around my cock.

“Take your shirt off,” I ask, and you comply. Your tits were beautiful, just gorgeous. Now it was my turn to recline the passenger seat, as you opened your mouth to swallow my cock.

The feeling was exquisite. It had been far too long since anyone had given me this kind of attention. Certainly not my wife. Your mouth was hot and wet and eager, your tongue doing acrobatics on my erect dick, swirling around the tip, pushing me closer and closer to the point of no return. As your head bobbed up and down, your hand was busy between your legs.

You looked up at me, my erection straining and bobbing wetly. “I think I could come again,” you said. I knew from your texts and emails that you weren’t usually multi-orgasmic.

It was tricky, in the little car, but we managed. You straddled my face, large breasts pressed against my flat stomach. I had a soft ass cheek in both hands. I cannot believe how wet your pussy is, how beautiful and sexy it looked from this vantage point, so up close and personal.

“Fuck my mouth” you said, “fuck my mouth and put your tongue on my clit, and I’ll do the rest.”

I complied, offering you my tongue as you opened your mouth wide, accepting the length of my cock.

I bucked my hips furiously, fucking your mouth like a wet pussy and you fingered yourself along with me, grinding on my outstretched tongue. It didn’t take me very long to come. I was way too turned on, too excited, too under your spell. I cried out loud, shooting my hot and sticky semen deep into your hungry mouth. You swallowed me, and swallowed again and again.

I could tell you were close as well. You held my softening dick in your mouth as you pressed your hard clit against my tongue, rocking back and forth, close, oh so close, but not quite there yet. I slapped your ass hard, alternating cheeks, and you whimpered. I slip a wet finger just inside your tight little anus, and that seemed to do the trick. You came sobbing, squeezing my head between your thighs until I couldn’t breath, my hand still beating your ass cheeks with all my strength as I struggled to keep my tongue on your clit.

Finally it was all over. Getting dressed in a parked car turned out to be considerably trickier than getting naked. Our bodies were spent and sticky. Big smiles were plastered across both of our faces.

“Wow,” you said, “That was intense.”

It certainly was. I could already feel a tingle in my dick, the beginnings of a new hardness. But the clock had other ideas. We both had to be getting back to our respective spouses, take showers, make excuses. We untangled, kissed, hug and squeeze, and kiss one last time.

The drive back home seemed longer than the drive down. I played the encounter over and over again in my mind; by the time I arrived back at the house, my cock was most definitely hard once more.

Wife was home already, putting groceries away. I was ready explain away my sweat as left over from my workout, your scent blamed on the gym, but and she didn’t even seem to notice my presence.

I pulled the shower curtain closed, letting the hot hot water fall on my naked body, stroking my cock and thinking of you.

Everything is the same as is was before. Except that it isn’t.


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